Aromatic diamine has been widely used in the fields of high-performance high polymers, such as p-phenylenediamine for the production of Kevlar, m-phenylenediamine for the production of Nomex, and 4,4'-oxydianiline for the production of Kapton; therefore, the potentiality of aromatic diamine has been more and more explored.
At the present, naphthalene-containing diamine, such as 1,5-nathalene diamine, is frequently used for the production of high-performance high polymers, such naphthalene-containing high polymers have better resistance to heat and better frigidity. Structures of naphthalene ether-containing diamines use dihydroxynaphthalene and p-chloronitrobenzene or p-fluoronitrobenzene to produce dinitro compound, before it is reduced to diaminide. Such prior art includes:
(A) U.S. Pat. No. 5,340,904 had disclosed various replacement of synthesis of bis(4-aminophenoxy) naphthalene, with its substituted position subsitution groups in naphthalene ring including (1,4), (1,5), (1,6), (1,7), (2,3), (2,6) and (2,7); PA1 (B) The U.S. Pat. No. 5,076,817 has mentioned the application of bis(4-aminophenoxy)naphthalene of substituted; PA1 (C) Chemical Abstrat: CA)Vol.117: 191511j has mentioned the synthesis of replacement positions of 1,6 of bis(4-aminophenoxy)naphthalene, using 1,6-dihydroxynaphthalene and p-chloronitrobenzene as preliminary ingredients. PA1 (D) Japanese Patent 1989 No. 33166 has mentioned that 2,6-bis(4-aminophenoxy)naphthalene with 2,6 substitutions in order to produce soluble polyimide. PA1 [1,3-bis(4-aminophenoxy)naphthalene] ##STR1## PA1 In structure (II), R.sub.1 is ##STR3## PA1 --(CH.sub.2).sub.m --(m.dbd.2--12); PA1 n is an integer between 10-600. PA1 In structure (III), R.sub.2 is ##STR5## PA1 Nn is an integer between 5-600. PA1 in structure (IV), R.sub.3 is ##STR7## PA1 n is an integer between 5-500. PA1 in structure (V), R.sub.3 is the same as that shown in the above structure (IV), n is an integer between 10-600. PA1 R.sub.1 is the same as shown in formula (II)
From the above prior art, it is known that there is no literature or report of substituted positions of 1,3 with bis(4-aminophenoxy), or related polymer technolgy. The 1,4-bis(aminophenoxy naththalene can not be produced from p-chloronitrobenzene and 1,4-dihydroxynaphthalene. However with the subject invention of 1,3-bis(4-aminophenoxy)naphthalene, high yield of dinitro compound could easily be produced from the reaction of 1,3-hydroxynaphthalene with p-fluoronitrobenzene or p-fluoronitrobenzene, which is then reduced to diamine compound, so it is a new type of compound.
The present invention synthesizes the new compound of 1,3-bis(4-aminophenoxy)naphthalene, then with this diamine to produce a series of aromatic polyamide, polyimide and various copoly(amideOimide)s, this series of polymers have excellent resistance to heat and good mechanical properties.
The molecular structure of 1,3-bis(4-aminophenoxy)naphthalene is as follows:
(1) diamine:
(2) polyamide: ##STR2##
(3) polyimide: ##STR4##
(4) polyamide-imide ##STR6##
(5) polyamide-imide ##STR8##
The preparation for the production of diamine and polymer:
The feature of the present invention is the position of bi-diphenylether group in naphthalene ring (1,3), such diamine has not been disclosed in previous literature, so it is a new compound.
(I) It can be produced from the condensation of 1,3-dihydroxynaphthalene and p-halonitrobenzene, which is then hydrogenated.
Its chemical reaction is shown as follows: ##STR9##
Condensation reaction can be accomplished by heating in an aprotic solvent under alkaline condition. Hydrogenating reaction can be made with metal reducing catalyst (such as palladium catalyst) with the introduction of hydrogen, or hydrazine can be used as the reducing agent to obtain the compound described in (I).
(2) polyamide (II)
Synthesis of polyamide of 4-aminophenoxy naphthalene is made by condensation polymerization of diamine (I) with dicarboxylic acid or activated dicarboxylic acid In direct reaction with dicarboxylic acid, tripheyl phosphite-pyidine can be used as a condensating agent. In the reaction with activated dicarboxylic acid, such as diacid chloride, direct reaction can be made using aprotic solvent such as DMAc (dimethylacetamide) or NMP(N-methglpyrrolidone).
Its reaction formula as follows: ##STR10##
In the formula: x indicates OH or Cl
(3) polyimide (III)
(II) is a series of polyimide containing naphthalene diphenylether group. It is produced by putting diamine (I) with aromatic anhydride in an appropriate organic solvent, which is condensed to have synthetic polyamic acid, then it is heated or added with a dehydrating agent (such as acetic anhydride), to proceed with polymerization condensation to have polyimide, its chemical reaction is shown in the following formula: ##STR11##
In the formula, R.sub.2 is the same as shown in above formula (III).
(4) plymide-polyimide (IV)
((IV) is dicarboxylic acid containing imide, produced by condensation of diamine (I) with Trimellitic Anhydride, which is then polymerized and condensed with a series of diamine.
In mole ratio. 1:2 of the above 1,3-bis(4aminophenoxy)naphthalene, which is heated in an appropriate solvent for dehydration and condensation in order to produce(VI), dicarboxylic acid (VI) is then condensed with a series of diamine. In the polymerization condensation of polymer IV, direct polymerization condensation of triphenyl phosphite/pyridine is recommended, its reaction formula as follows: ##STR12##
In the formula, R.sub.3 is the same as shown in the above formula (IV).
(5) polyamide-polyimide (V)
(V)) is a series of polyamide-polyimide (V) related to Trimellitic Anhydride. Firstly, a series of diamine is condensed with Trimellitic Anhydride to obtain a series of dicarboxylic acid (VII) containing polyimide, diamine (I) is then mixed with dicarboxylic acid (VII) for polymerization condensation reaction to obtain polymer (V), tripheyl phosphite-pyidine is recommended as the condensing agent, its reaction formula is as follows: ##STR13##
In the formula, R.sub.3 is the same as shown in above (IV).